Pumpkin Whoopie Pies with Cinnamon Cream Filling

There’s something about pumpkin season that makes every day feel a little warmer and sweeter. These Pumpkin Whoopie Pies are soft, cake-like cookies filled with a fluffy cinnamon cream filling that tastes like fall in every bite. They’re the perfect treat for Thanksgiving dessert tables, bake sales, holiday gatherings, or simply enjoying with a hot cup of coffee on a chilly afternoon.

The pumpkin keeps the cookies incredibly moist while warm spices add that classic autumn flavor everyone loves. Sandwiched together with a rich cinnamon filling, they look impressive but are surprisingly easy to make. Whether you’re baking for family, friends, or just because pumpkin season is calling your name, these homemade whoopie pies are guaranteed to disappear fast.

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Why You’ll Love These Pumpkin Whoopie Pies

• Soft and fluffy texture – These cake-like pumpkin cookies are incredibly tender and melt in your mouth with every bite.
• Perfect fall flavor – Pumpkin, cinnamon, and warm spices come together to create a cozy autumn dessert everyone loves.
• Creamy cinnamon filling – The sweet, fluffy filling adds the perfect contrast to the soft pumpkin cakes.
• Great for gatherings – These handheld treats are easy to serve at Thanksgiving dinners, fall parties, bake sales, and potlucks.
• Make-ahead friendly – Prepare them a day in advance and store them in the refrigerator until you’re ready to serve.
• Beautiful bakery-style dessert – They look impressive enough for special occasions but are simple enough for beginner bakers to make at home.

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Ingredients Method Notes

Ingredients

  

• For the Pumpkin Cookies:
• * 2 cups all-purpose flour
• * 1 teaspoon baking powder
• * 1 teaspoon baking soda
• * ½ teaspoon salt
• * 1 teaspoon ground cinnamon
• * ½ teaspoon ground ginger
• * ¼ teaspoon ground nutmeg
• * ¼ teaspoon ground cloves
• * ½ cup unsalted butter softened
• * ¾ cup brown sugar
• * ¼ cup granulated sugar
• * 1 large egg
• * 1 cup pumpkin puree
• * 1 teaspoon vanilla extract
• For the Cinnamon Cream Filling:
• * ½ cup unsalted butter softened
• * 2 cups powdered sugar
• * 1 teaspoon vanilla extract
• * 1 teaspoon ground cinnamon
• * 1 to 2 tablespoons heavy cream or milk

Method

 

1. Preheat the oven to 350°F. Line two baking sheets with parchment paper.
2. In a medium bowl, whisk together the flour, baking powder, baking soda, salt, cinnamon, ginger, nutmeg, and cloves.
3. In a large bowl, beat the butter, brown sugar, and granulated sugar until light and fluffy.
4. Add the egg, pumpkin puree, and vanilla extract. Mix until smooth.
5. Gradually add the dry ingredients to the wet ingredients and mix just until combined.
6. Scoop tablespoon-sized portions of batter onto the prepared baking sheets, spacing them about 2 inches apart.
7. Bake for 10 to 12 minutes or until the tops spring back lightly when touched.
8. Allow the cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
9. To make the filling, beat the butter until creamy. Add the powdered sugar, vanilla, cinnamon, and enough cream to create a smooth, fluffy filling.
10. Spread or pipe the filling onto the flat side of half the cookies.
11. Top with the remaining cookies to create sandwich cookies.
12. Chill for 20 minutes before serving for the best texture.

Notes

* Store in an airtight container in the refrigerator for up to 4 days.
* Let sit at room temperature for 10 to 15 minutes before serving.
* Extra filling can be refrigerated and used on cupcakes or cookies.

Step 1: Prepare the Baking Sheets

Preheat your oven to 350°F (175°C). Line two large baking sheets with parchment paper and set them aside. This helps prevent sticking and ensures even baking.

Step 2: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking powder, baking soda, salt, cinnamon, nutmeg, ginger, and cloves. Combining the spices now helps distribute the flavors evenly throughout the batter.

Step 3: Cream the Butter and Sugars

In a large mixing bowl, beat the softened butter with the brown sugar and granulated sugar until the mixture becomes light and fluffy. This creates a soft texture and adds air to the batter.

Step 4: Add the Wet Ingredients

Mix in the egg, pumpkin puree, and vanilla extract until smooth and fully combined. The pumpkin gives the cookies their signature moisture and rich fall flavor.

Step 5: Combine Wet and Dry Mixtures

Gradually add the dry ingredients to the pumpkin mixture, mixing just until no streaks of flour remain. Be careful not to overmix, as this can make the cookies dense.

Step 6: Scoop the Batter

Using a cookie scoop or tablespoon, drop evenly sized portions of batter onto the prepared baking sheets, leaving space between each cookie for spreading.

Step 7: Bake Until Set

Bake for 10 to 12 minutes, or until the tops spring back lightly when touched. Remove from the oven and allow the cookies to cool on the baking sheet for a few minutes before transferring to a wire rack.

Step 8: Make the Cinnamon Cream Filling

While the cookies cool, beat together softened butter, powdered sugar, vanilla extract, cinnamon, and a splash of cream until light and fluffy. The filling should be smooth and easy to spread.

Step 9: Assemble the Whoopie Pies

Turn half of the cooled cookies upside down. Spread or pipe a generous amount of cinnamon cream filling onto each one, then top with a second cookie to create sandwiches.

Step 10: Chill and Serve

For the best texture, chill the assembled whoopie pies for about 20 minutes before serving. Enjoy immediately or store in an airtight container in the refrigerator until ready to eat.

The Bottom Line

If these Pumpkin Whoopie Pies have you in the mood for more cozy fall baking, there are plenty of delicious seasonal treats to explore next. Create the perfect holiday spread with these Thanksgiving Snack Board Ideas, or fill your cookie tray with even more festive favorites from this collection of Thanksgiving Cookie Ideas.

Looking for treats that are perfect for sharing, gifting, or selling? You’ll find plenty of inspiration in these crowd-pleasing Fall Bake Sale Treats. Pumpkin lovers should also try these soft and flavorful Pumpkin Pudding Cookies, packed with warm autumn spices.

For an elegant dessert that highlights the flavors of the season, don’t miss these Maple Baked Pears with Candied Pecans. Whether you’re planning a holiday gathering or simply enjoying fall baking at home, these recipes will keep your kitchen smelling amazing all season long.